Red azo dye and process of making same.



UNITED STATES PATENT OFFICE.

JOHN HAGENBAOH, OF BASLE, SWITZERLAND, ASSIGNOR TO ANILINE COLOUR ANDEXTRACT WORKS, FORMERLY JOHN R. GEIGY, OF

BASLE, SWITZERLAND.

Specification of Letters Patent.

Patented Jan. 2, 1906.

Application filed June 29,1905. Serial No. 267,676. (Specimens) 1'0 a/ZZwhom it may concern.-

Be it known that I, JOHN HAGENBAGI-I,

Ph. D., a citizen of the Swiss Republic, residing at Basle, Switzerland,have invented certain new and useful Improvements in Red Azo Dyestuffsand Processes of Making the Same, of which the following is aspecification.

Of i .0 derivatives from amidonaphthols only the diazo compound of the2-amido-3- naphthol-6-sulfonic acid has been coupled until now with1-phenyl-5-pyrazolones which are not substituted in position four, (German Patent No. 134,162.)

Now I have found that the diazo bodies of the 1-2 and 2-1-amidonaphtholsulfonic acids which according to the process described in theapplication for United States Letters Patent, Serial No. 226,619, filedSeptember 30, 1904,can be produced in a technical way more easily thanthe 2-diazo3-naphthol-6- sulfonic acid, combine very promptly with theabove-mentioned 1-phenyl-5-pyrazolones yielding very valuable dyestuffs.The new coloring-matters thus obtained are darkbrown powders with slightmetallic luster, soluble in water with an orange-yellow'to reddish-browncolor, turning into yellowish red to bluish red by adding acetic acid.In concentrated sulfuric acid they dissolve with a bright-orange to redcolor and distinguish themselves from the coloring-matters of theZ-diazo-3-naphthol-6-sulfonic acid whose dyeings on wool treated withpotassium bichromate, giving only brown-red shades, in the mostadvantageous way by the bright yellowish-red to bluish-redtints of theirdyeings treated with a chromium compound.

In carrying out my process practically I can proceed as follows, theparts being by weight: twenty-five parts of powdered and dried diazocompound from l-amido-2-naphtholi-sulfonic acid are slowly introducedwhile stirring into a solution of eighteen parts of1-phenyl-3-methyl-5-pyrazolone in about five hundred parts of water,twelve parts of caustic-soda lye, (40 Baum,) and fifteen parts of sodiumcarbonate. After a few hours the combination is accomplished. Thecoloring-matter is then precipitated by the addition of common saltfiltered off and dried. It forms a dark-brown shiny powder and dissolvesin water with an orange-yellow color, which upon addition of acetic acidchanges into a brilliant red. In concentrated sulfuric acid it dissolveswith magenta color. If the coloring is precipitated from the alkalinesolution by addition of a small surplus of an acid instead of commonsalt, it is obtained in the form of a bright-red crystalline powder.

The new coloring-matter dyes wool from acid-bath reddish-brown yellow,which shade by subsequent treatment with a chromium compound changes tocrimson-red, distinguished for great fastness to the action of light andthe processes of milling and pot ting.

The process proceeds in an analogous manner if otherdiazonaphtholsulfonic acids or if other phenylpyrazolones are used.

In the following small table I give the shades of the dyeings on wool ofsome more of the new dyestuffs from an acid-bath and after treatmentwith potassium bichromate;

Dyestuff produced by Dyes wool After treatment combination of di-Withfrom acidwith potassium azotized. bath. bichromatc.

1-amido-2-naphthol-6- Y ell owish Brownish-yellow sulfonic acid. brown.red.

1-amido-2-naphthol-7- Y e 11 owish Yellowish-b l u e sulfonic acid. 5brown. red.

1-amido-2-naphthol-3- T5 R e d d i s h Blue-red.

6-disulfonic acid. brown.

1-amido-2-naphtho1-4- g R e d d i s h Yellowish-b l u e 6disu1fonicacid. p v e l l o w red.

3;, brown .2

2-amido-1-naphtl1o1-4- 5 v i o 1 e t Yellowish red.

sulfonic acid. brown.

2-amido-1-naphthol-5- 7;, Y e llowish- Blue-red.

sulfonic acid. g red brown.

2-amido-1-naphthoL3- Q V i o l e t Yellowish red.

G-disulfonic acid. H brown.

2-amido-1-naphthol-4- R e d d i s h Bi'ownish b 1 u e S-disulfonic acid.yellow. re

Having now described my invention, what I claim is 1. The process forproducing red azo dyestuffs by combining the diazo derivatives of orthoamidonaphthol sulfonic acids with 1- phenyl-5-pyrazolones capable tocombine in position four, substantially as set forth.

2. The process for producing a red azo dyestufi by combining the diazoderivative of 1- amido-2-naphtol4-sulfonic acid with1-phenyl-3-methyl-5-pyrazolone substantially as set forth.

3. The herein-described new azo dyestufis let-brown shades, changinginto yellowish red to bluish red when treated after dyeing with chromiumcompounds substantially as set forth.

4:. The herein-described new azo dyestufls produced by combining thediazo derivative from 1-amido-2-naphthol-4-sulfonic acid with1-phenyl-3-methyl-5-pyrazolone, forming a dark-brown shiny powder,soluble in water with an orange-yellow color, turning into a brilliantred by addition of acetic acid, soluble in concentrated sulfuric acidwith magenta color and yielding on wool from acidbathreddish-brown-yellow shades changing into crimson-red when treated afterdyeing with chromium compounds substantially as set forth.

In testimony whereof I have signed this specification in the presence oftwo subscribing witnesses.

JOHN HAGENBACH.

Witnesses ALB. GRAs'rE, GEO. GIFFoRD.

